Phosphine-Mediated Reaction of 3-Alkyl Allenoates and Diaryl 1,2-Diones: Efficient Diastereoselective Synthesis of Fully Substituted Cyclopentenones

Abstract

An efficient phosphine-mediated diastereoselective synthesis of substituted cyclopentenones from 3-alkyl allenoates and diaryl 1,2-diones is described.

Facile Diastereoselective Synthesis of Highly Substituted Alkylene‐oxetanes from 3‐Alkyl Allenoates and Diaryl 1,2‐Diones/α‐Ketoamides Mediated by DBU

“…We have recently investigated the reaction of 3‐alkyl allenoates and diaryl‐1,2‐diones in the presence of triaryl phosphines, leading to fully substituted cyclopentenones (Scheme , b) . Lewis base‐catalyzed [3+2] and [4+2] annulation reactions of allenoates have emerged as powerful tools for the synthesis of a wide variety of carbo‐cyclic or heterocyclic compounds .…”

Organophosphine-Catalyzed [4C+X] Annulations

“…In 2013, the group of Huang disclosed an unprecedented phosphine-catalyzed [4+2] annulation of γ -substituted allenoates 82 with 2-arylidene-1 H -indene-1,3(2 H )-diones ( Scheme 26 ) [ 63 ]. Differently from the previously reported annulation reactions that γ -substituent allenoates had participated in before [ 64 , 65 , 66 , 67 , 68 ], the γ -benzyl allenoates firstly serves as a new type of C 4 synthon in this novel [4+2] cyclization process. With this method, highly substituted spiro-[4.5]-dec-6-ene skeletons 83 could be powerfully constructed in excellent yields with complete regioselectivity and high diastereoselectivity.…”

Chemo‐Selective Synthesis of Tetrazole‐Containing Cyclopentenyl Phosphanylidene Dicarboxylates

“…Tetrazole is one of the most interesting synthetic scaffolds in medicinal chemistry . Addition of triphenylphosphine to acetylenic esters produces a 1,3‐dipole moiety which can be trapped by many suitable acceptors such as alkenes, alkynes, aldehydes, etc., in order to generate a wide range of new compounds . The generated zwitterionic species can be used to produce the carbocyclic systems in a Michael's reaction mode .…”